4-Fluoroephedrine (4-FEP) is a "novel psychoactive substance" and substituted β-hydroxyamphetamine derivative related to ephedrine.[1][2][3]
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| Other names | 4-FEP; 4-Fluoro-β-hydroxy-N-methylamphetamine |
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| Formula | C10H14FNO |
| Molar mass | 183.226 g·mol−1 |
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Pharmacology
editSimilarly to other amphetamines, 4-fluoroephedrine acts as a monoamine reuptake inhibitor and monoamine releasing agent.[3][4] It specifically acts as a selective norepinephrine releasing agent.[3][4] In contrast to many other amphetamines, but similarly to most cathinones, 4-fluoroephedrine lacks affinity for the human trace amine-associated receptor 1 (hTAAR1).[3][4][5]
Chemistry
edit4-Fluoroephedrine, also known as 4-fluoro-β-hydroxy-N-methylamphetamine, is a substituted phenethylamine, amphetamine, and β-hydroxyamphetamine derivative.[6][1] It is the non-enantiopure 4-fluoro analogue of ephedrine.[6][1]
The synthesis of 4-fluoroephedrine has been described.[7]
It can serve as a precursor in the synthesis of 4-fluoromethamphetamine (4-FMA).[3]
The predicted log P (XLogP3) of 4-fluoroephedrine is 1.0.[6] For comparison, the predicted log P of ephedrine is 0.9.[8]
History
edit4-Fluoroephedrine was first described in the scientific literature by 1991.[7] The next mention of it in the literature was in 2013, when it was identified as a "novel psychoactive substance".[9] The pharmacology of 4-fluoroephedrine was characterized in 2015.[3][4]
Other drugs
edit4-Fluoroephedrine is known to be a metabolite of 4-fluoromethcathinone (4-FMC; flephedrone).[10][11]
References
edit- ^ a b c King LA (2014). "New phenethylamines in Europe". Drug Test Anal. 6 (7–8): 808–818. doi:10.1002/dta.1570. PMID 24574327.
- ^ Corkery JM, Schifano F, Martinotti G (March 2020). "How deaths can help clinicians and policy-makers understand the risks of novel psychoactive substances". Br J Clin Pharmacol. 86 (3): 482–498. doi:10.1111/bcp.14183. PMC 7080619. PMID 31770457.
- ^ a b c d e f Rickli, Anna (2016). Pharmacology of novel psychoactive substances (Thesis). doi:10.5451/UNIBAS-006616893.
- ^ a b c d Rickli A, Hoener MC, Liechti ME (March 2015). "Monoamine transporter and receptor interaction profiles of novel psychoactive substances: para-halogenated amphetamines and pyrovalerone cathinones". Eur Neuropsychopharmacol. 25 (3): 365–376. doi:10.1016/j.euroneuro.2014.12.012. PMID 25624004.
- ^ Simmler LD, Buchy D, Chaboz S, Hoener MC, Liechti ME (April 2016). "In Vitro Characterization of Psychoactive Substances at Rat, Mouse, and Human Trace Amine-Associated Receptor 1". J Pharmacol Exp Ther. 357 (1): 134–144. doi:10.1124/jpet.115.229765. PMID 26791601.
- ^ a b c "1-(4-Fluorophenyl)-2-(methylamino)propan-1-ol". PubChem. Retrieved 12 September 2024.
- ^ a b Mullen AJ (1991). The synthesis and pharmacology of ephedrine analogues (Thesis). Retrieved 12 September 2024.
- ^ "Ephedrine". PubChem. Retrieved 12 September 2024.
- ^ Archer JR, Dargan PI, Chan WL, Hitchings A, Hudson S, Wood DM (2013). "201. Trend analysis of novel psychoactive substances detected in pooled urine samples from street urinals over six months" (PDF). Clinical Toxicology. 51 (7).
- ^ Uralets V, Rana S, Morgan S, Ross W (June 2014). "Testing for designer stimulants: metabolic profiles of 16 synthetic cathinones excreted free in human urine". J Anal Toxicol. 38 (5): 233–241. doi:10.1093/jat/bku021. PMID 24668489.
- ^ Fan SY, Zang CZ, Shih PH, Ko YC, Hsu YH, Lin MC, Tseng SH, Wang DY (October 2020). "A LC-MS/MS method for determination of 73 synthetic cathinones and related metabolites in urine". Forensic Sci Int. 315: 110429. doi:10.1016/j.forsciint.2020.110429. PMID 32784041.